EP0455657B1 - Melanges tensio-actifs - Google Patents

Melanges tensio-actifs Download PDF

Info

Publication number
EP0455657B1
EP0455657B1 EP90901802A EP90901802A EP0455657B1 EP 0455657 B1 EP0455657 B1 EP 0455657B1 EP 90901802 A EP90901802 A EP 90901802A EP 90901802 A EP90901802 A EP 90901802A EP 0455657 B1 EP0455657 B1 EP 0455657B1
Authority
EP
European Patent Office
Prior art keywords
mixtures
alkyl
contain
group
alkylol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90901802A
Other languages
German (de)
English (en)
Other versions
EP0455657A1 (fr
Inventor
Reinhard Müller
Bernd Fabry
Jutta Thul
Klaus-Dieter Wisotzki
Karl Giede
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT90901802T priority Critical patent/ATE91406T1/de
Publication of EP0455657A1 publication Critical patent/EP0455657A1/fr
Application granted granted Critical
Publication of EP0455657B1 publication Critical patent/EP0455657B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/06—Ether- or thioether carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/126—Acylisethionates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides

Definitions

  • the invention relates to surface-active mixtures with low skin stress.
  • aqueous preparations In order to enhance the cleaning action of aqueous preparations, they usually contain surface-active compounds. However, an increased cleansing effect is usually associated with increased skin stress. This is especially true for the important class of anionic surfactants.
  • ampholytic and nonionic surfactants are often characterized by improved skin tolerance compared to anionic surfactants.
  • these classes of surfactants cannot be used as a replacement for anionic surfactants for many areas of application because they do not achieve their properties in terms of their cleaning action.
  • the foam formation desired for shampoos is generally not guaranteed if amphoteric surfactants are used exclusively or predominantly.
  • the surface-active internal ether sulfonates (A) are the subject of German patent application P 37 25 030.2.
  • the compounds are accessible by reacting the unsaturated fatty alkyl or fatty alkyl polyoxyalkyl ester with SO3 and then working up the reaction product with aqueous alkali metal, alkaline earth metal or ammonium hydroxide.
  • SO3 unsaturated fatty alkyl or fatty alkyl polyoxyalkyl ester
  • ammonium hydroxide aqueous alkali metal, alkaline earth metal or ammonium hydroxide
  • the internal ether sulfonates (A) are contained in the surface-active aqueous mixture in amounts of 1 to 99% by weight, based on the total amount of the anionic surfactants.
  • Preferred internal ether sulfonates (A) are the ethoxylated compounds in which x represents a number from 3 to 15, in particular from 5 to 10.
  • Fatty alcohol ether sulfates are to be understood as meaning the sulfates of the adducts of ethylene oxide (EO) and / or propylene oxide (PO) with saturated and / or unsaturated, linear and / or branched fatty alcohols, which are obtainable by known processes.
  • the fatty alcohols on which the fatty alcohol ether sulfates are based can be pure compounds. However, it is usually preferred to use mixtures of different fatty alcohols obtained from native raw materials such as fats and oils. These fatty alcohols can be reacted with the alkylene oxides, for example under pressure and in the presence of catalysts, to give fatty alcohol alkoxylates.
  • the desired fatty alcohol ether sulfates are finally obtained by reacting the fatty alcohol alkoxylates with, for example, sulfur trioxide or chlorosulfonic acid and subsequent neutralization, for example with alkali metal, alkaline earth metal, aluminum or ammonium hydroxides.
  • Preferred fatty alcohol ether sulfates (B1) are compounds of the formula (III), RO- (C m H 2m O) v -SO3X (III) in which R is a saturated or olefinically unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms, m 2 or 3, v is a number from 1 to 15 and X is hydrogen, an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl - Or alkylolammonium group with 1 to 4 carbon atoms in each alkyl or alkylol group.
  • R is a saturated or olefinically unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms, m 2 or 3
  • v is a number from 1 to 15
  • X is hydrogen, an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl - Or alkylolammoni
  • R is a saturated alkyl radical with 8 to 16 carbon atoms
  • m 2
  • v is a number from about 2 to 10
  • X is sodium, potassium, magnesium, aluminum, ammonium or a mono-, di- or triethanolammonium group.
  • Preferred fatty alcohol sulfates (B2) are compounds of the formula (IV) RO-SO3X (IV) in which R is a saturated or olefinically unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms and X is hydrogen, an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl or alkylolammonium group having 1 to 4 carbon atoms in each alkyl - or alkylol group.
  • R is a saturated or olefinically unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms and X is hydrogen, an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl or alkylolammonium group having 1 to 4 carbon atoms in each alkyl - or alkylol group.
  • R is a saturated alkyl radical having 8 to 16 carbon atoms and X are sodium, potassium, magnesium, aluminum, ammonium or a mono-, di- or triethanolammonium group are particularly preferred.
  • Preferred ether carboxylic acids (B3) are compounds of the formula (V) RO- (C m H 2m O) v -CH2-COOX (V) in which R is a saturated or olefinically unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms, m 2 or 3, v is a number from 1 to 15 and X is hydrogen, an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl - Or alkylolammonium group with 1 to 4 carbon atoms in each alkyl or alkylol group.
  • R is a saturated alkyl radical with 8 to 16 carbon atoms
  • m 2
  • v is a number from about 5 to 12, in particular about 10
  • X is sodium, magnesium, aluminum, ammonium or a mono- , Di- or triethanolammonium group.
  • Ether carboxylic acids of the type mentioned are sold, for example, by the company CHEM-Y under the name "Akypo (R) ".
  • the sulfosuccinic acid semiesters are particularly preferred.
  • Z ' is an alkali metal, an alkaline earth metal, aluminum, an ammonium group or an alkyl or alkylolammonium group with 1 to 4 carbon atoms in each alkyl or alkylol group.
  • acyl sarcosides which can be used according to the invention as a further class of anionic surfactants are reaction products of fatty acids with N-methylglycine with the general formula R-CO-N (CH3) -CH2-COOH, where R-CO is a fatty acyl radical with 8-22 C atoms, preferably with 10- 18 carbon atoms.
  • the acyl taurides are reaction products of fatty acid chlorides with N-methyl taurine with the general formula R-CO-N (CH3) -CH2-CH2-SO3Na, where R-CO is a fatty acyl residue with 8-22 carbon atoms, especially with 10 -18 carbon atoms, and instead of sodium other counterions such as other alkali metal ions, alkaline earth metal ions or ammonium ions can be present.
  • Acyl isethionates are usually prepared by reacting fatty acid chlorides with sodium isethionate and have the general formula R-CO-O-CH2-CH2-SO3Na, where R-CO is a fatty acyl radical with 8-22 C atoms, in particular with 10-18 C atoms, represents and in place of sodium other counterions such as other alkali metal ions, alkaline earth metal ions or ammonium ions may be present.
  • ⁇ -olefin sulfonates are usually prepared by sulfonation of ⁇ -olefins with SO3 and subsequent hydrolysis of the sultones thus obtained.
  • Secondary alkyl sulfonates are accessible by sulfochlorination or sulfoxidation of linear paraffins and have the general formula R-CH (SO3Na) -R ', where R and R' are linear alkyl groups with 1-10 C atoms, the sum of the C atoms in R and R 'is 10 to 20, and other counterions such as other alkali metal ions, alkaline earth metal ions or ammonium ions may also be present in place of the sodium.
  • the surface-active mixtures according to the invention contain a total of about 2-50% by weight of anionic surfactants. A content of 5-30% by weight is preferred.
  • the surface-active mixtures according to the invention can additionally contain 0.5-20% by weight, in particular 1-10% by weight, of ampholytic and / or zwitterionic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C8-C18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. Atoms in the alkyl group.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO (-) - or -SO3 (-) group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example that Kokosacylaminopropyl-dimethylammoniumglycinat, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each with 8 to 18 carbon atoms in the alkyl or acyl group, and the Kokosacylaminoethylhydroxyethylcarboxymethylglycinat.
  • the skin-protecting properties of the agents according to the invention come into their own particularly when they are formulated in such a way that they have a pH value in the vicinity of the neutral point. Agents with pH values in the range from 5.5 to 7.5, in particular from 6.5 to 7.5, are therefore preferred.
  • the agents according to the invention can be used in a variety of consumer products such as hair shampoos, bubble baths, shower baths, liquid soaps and manual dishwashing detergents.
  • these products contain the usual ingredients such as emulsifiers, oil components, fats and waxes, solubilizers, thickeners, superfatting agents, biogenic agents, film formers, fragrances, dyes, pearlescent agents, foam stabilizers, preservatives and pH regulators.
  • emulsifiers oil components, fats and waxes, solubilizers, thickeners, superfatting agents, biogenic agents, film formers, fragrances, dyes, pearlescent agents, foam stabilizers, preservatives and pH regulators.
  • the substances customary in cosmetic preparations such as, for. B. fatty acid partial glycerides, fatty acid sorbitan partial esters and their ethoxylates, soaps, fatty alcohol polyglycol ethers, lanolin, wool fatty alcohols and alkyl phosphates can be used.
  • Common oil components are substances such as paraffin oil, vegetable oils, fatty acid esters, squalane and 2-octyldodecanol, while fats and waxes are used, for example, as walrus, beeswax, montan wax, paraffin and cetylstearyl alcohol.
  • Low monohydric or polyhydric alcohols such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol, 1,3-butylene glycol and diethylene glycol are usually used as solubilizers.
  • Substances such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides can be used as superfatting agents, the latter also simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar gum, agar agar, alginates and tyloses, and also carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone and finally electrolytes such as sodium chloride , if desired in combination with alkyl ether sulfates.
  • polysaccharides in particular xanthan gum, guar gum, agar agar, alginates and tyloses, and also carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone and finally electrolytes such as sodium chloride , if desired in combination with alkyl ether
  • Biogenic active substances are to be understood as plant extracts, protein breakdown products and vitamin complexes.
  • Common film formers are, for example, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Particularly suitable pearlescent agents are glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • fragrances and substances which serve to adjust the pH of the agents are fragrances and substances which serve to adjust the pH of the agents.
  • the mixtures according to the invention are preferably used in products which are used for washing, dyeing, waving or rinsing hair.
  • the mixtures are particularly suitable for shampoos for washing hair.
  • the swelling of the pig epidermis served as a measure of the skin tolerance of the surfactant mixtures.
  • the required epidermis was obtained immediately after young pigs were slaughtered and stored frozen.
  • the Q value of the water-treated skin is therefore by definition 0%; negative values indicate anti-swelling properties.
  • the results of the swelling measurements are summarized in the following table.
  • the amount stated relates to the total amount of 2% anionic surfactant.
  • the foaming behavior of the surfactants and surfactant mixtures was determined using a motorized blow-foam apparatus based on DIN 53902.
  • 340 ml of surfactant solution (2% by weight of active substance in tap water from Düsseldorf-Holthausen at 18 ° dH) were prepared.
  • the foam was generated at room temperature with a perforated plate (holes of 1 mm diameter, 10 impacts at a frequency of 50 impacts / min, 13 cm stroke); it was very fine-pored and thus largely corresponded to a foam that formed on the head when shampooing.
  • the measurements were carried out as a duplicate determination without grease contamination of the surfactant solution.
  • This mixture was diluted with water and also used in the form of a solution with 2% by weight of active substance.
  • the following amounts of foam were measured: after 1 minute: 240 ml after 3 minutes: 210 ml after 5 minutes: 190 ml
  • the measured amounts of foam of the surfactant solutions according to the invention are given in the following table in percent based on the amount of foam of the comparison substance.
  • Aqueous systems were investigated which contained 1.6% by weight of active substance of the surfactant mixture M5 and 0.4% by weight of active substance of the ampholytic / zwitterionic surfactant Z.
  • the table also shows the value for a mixture which contains 2% by weight of active substance of the binary surfactant mixture M5.
  • the foaming behavior of these ternary surfactant mixtures was determined in the same way as for the binary surfactant mixtures.
  • the aqueous mixtures contained 1.6% by weight of active substance of the binary surfactant mixture M5 and 0.4% by weight of active substance of the third surfactant component Z.
  • the measured amounts of foam of the surfactant solutions according to the invention are given in the following table in percent based on the amount of foam of the comparison substance.
  • the table also shows the value for a mixture which contains 2% by weight of active substance of the binary surfactant mixture M5.
  • the hair After the treatment with this shampoo, the hair had excellent wet combability and excellent dry combability.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Materials Engineering (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Claims (16)

  1. Mélanges aqueux de tensioactifs, renfermant au moins deux surfactifs anioniques différents, caractérisés en ce qu'ils renferment comme tensioactifs anioniques
    a) un mélange d'éthersulfonates tensioactifs internes (A), qui se compose en totalité ou en majeure partie de composés des formules (I) et/ou (II)
    Figure imgb0021
    Figure imgb0022
     ou de leurs sels de métaux alcalins, de métaux alcalino-terreux, d'aluminium et d'ammonium, formules dans lesquelles y et z sont égaux à 0 ou à des nombres allant de 1 à 18, p est égal à 0, à 1 ou à 2 et la somme (y+z+p) équivaut à un nombre allant de 12 à 18, x est égal à 0 ou à un nombre entier allant jusqu'à 30 et n peut être un nombre entier allant de 2 à 4,
    et
    b) au moins un autre composé (B) sélectionné dans le groupe des éthersulfates d'alcools gras, sulfates d'alcools gras, acides éthercarboxyliques, esters d'acide sulfosuccinique , acylsarcosides, acyltaurides, acyliséthionates, alphaoléfinesulfonates et alkylsulfonates secondaires.
  2. Mélanges selon la revendication 1, caractérisés en ce que dans les composés (A) conformes à la formule (I) ou (II), n est égal à 2 et x équivaut à un nombre entier allant de 3 à 15, en particulier de 5 à 10.
  3. Mélanges selon l'une des revendications 1 ou 2, caractérisés en ce qu'ils renferment comme composant (A), des éthersulfonates internes avec (y+z+p) = 14 et x = 10.
  4. Mélanges selon l'une des revendications 1 à 3, caractérisés en ce qu'ils renferment des composés (A) conformes à la formule (I) ou (II), en proportions allant de 1 à 99 % en poids, par rapport à la quantité totale des tensioactifs anioniques.
  5. Mélanges selon l'une des revendications 1 à 4, caractérisés en ce qu'ils renferment comme tensioactif anionique (B1) des éthersulfates d'alcools gras conformes à la formule (III),

            R-O-(CmH2mO)v-SO₃X   (III)

    dans laquelle R représente un radical alkyle linéaire ou ramifié, saturé ou à insaturation oléfinique, comportant 8 à 22 atomes de C, m est égal à 2 ou à 3, v correspond à un nombre allant de 1 à 15 et X est l'hydrogène, un métal alcalin, un métal alcalino-terreux, l'aluminium, un groupe ammonium ou un groupe alkyl- ou alkylolammonium comportant 1 à 4 atomes de C dans chaque groupe alkyle ou alkylol.
  6. Mélanges selon l'une des revendications 1 à 5, caractérisés en ce qu'ils renferment les tensioactifs anioniques (A) et (B1) dans un rapport de quantités compris entre environ 10:90 et environ 70:30, en particulier entre 20:80 et 60:40.
  7. Mélanges selon l'une des revendications 1 à 6, caractérisés en ce qu'ils renferment comme tensioactif anionique (B2), des sulfates d'alcools gras conformes à la formule (IV),

            R-O-SO₃X   (IV)

    dans laquelle R représente un radical alkyle linéaire ou ramifié, saturé ou à insaturation oléfinique, comportant 8 à 22 atomes de C et X est l'hydrogène, un métal alcalin, un métal alcalino-terreux, l'aluminium, un groupe ammonium ou un groupe alkyl- ou alkylolammonium comportant 1 à 4 atomes de C dans chaque groupe alkyle ou alkylol.
  8. Mélanges selon l'une des revendications 1 à 7, caractérisés en ce qu'ils renferment les tensioactifs anioniques (A) et (B2) dans un rapport de quantités compris entre environ 10:90 et environ 50:50, en particulier entre 10:90 et 30:70.
  9. Mélanges selon l'une des revendications 1 à 8, caractérisés en ce qu'ils renferment comme tensioactif anionique (B3), des acides éthercarboxyliques conformes à la formule (V),

            R-O-(CmH2mO)v-CH₂-COOX   (V)

    dans laquelle R représente un radical alkyle linéaire ou ramifié, saturé ou à insaturation oléfinique, comportant 8 à 22 atomes de C, m est égal à 2 ou à 3, v correspond à un nombre allant de 1 à 15 et X est l'hydrogène, un métal alcalin, un métal alcalino-terreux, l'aluminium, un groupe ammonium ou un groupe alkyl- ou alkylolammonium comportant 1 à 4 atomes de C dans chaque groupe alkylol.
  10. Mélanges selon l'une des revendications 1 à 9, caractérisés en ce qu'ils renferment les tensioactifs anioniques (A) et (B3) dans un rapport de quantités compris entre environ 10:90 et environ 90:10, en particulier entre 20:80 et 80:20.
  11. Mélanges selon l'une des revendications 1 à 10, caractérisés en ce qu'ils renferment comme tensioactif anionique (B4) des esters d'acide sulfosuccinique conformes à la formule (VI),
    Figure imgb0023
     dans laquelle R représente un radical alkyle linéaire ou ramifié, saturé ou à insaturation oléfinique, comportant 8 à 22 atomes de C, m est égal à 2 ou à 3, w correspond à 0 ou à un nombre allant de 1 à 15 et Z est un métal alcalin, un métal alcalino-terreux, l'aluminium, un groupe ammonium ou un groupe alkyle ou alkylolammonium comportant 1 à 4 atomes de C dans chaque groupe alkyle ou alkylol et Z' représente un métal alcalin, un métal alcalino-terreux, l'aluminium, un groupe ammonium ou un groupe alkyl- ou alkylolammonium comportant 1 à 4 atomes de C dans chaque groupe alkyle ou alkylol ou un groupe R.
  12. Mélanges selon l'une des revendications 1 à 11, caractérisés en ce qu'ils renferment les tensioactifs anioniques (A) et (B4) dans un rapport de quantités compris entre environ 10:90 et environ 90:10, en particulier entre 20:80 et 80:20.
  13. Mélanges selon l'une des revendications 1 à 12, caractérisés en ce qu'ils renferment en plus 0,5 à 20 % en poids, en particulier 1 à 10 % en poids de tensioactifs ampholytes et/ou zwitterioniques, chacun par rapport à la totalité du mélange.
  14. Mélanges selon l'une des revendications 1 à 13, caractérisés en ce qu'ils présentent un pH de 5,5 à 7,5, en particulier de 6,5 à 7,5.
  15. Mélanges selon l'une des revendications 1 à 14, caractérisés en ce qu'ils sont formulés comme shampooing.
  16. Utilisation des mélanges selon l'une des revendications 1 à 15 pour le traitement des cheveux.
EP90901802A 1989-01-25 1990-01-17 Melanges tensio-actifs Expired - Lifetime EP0455657B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90901802T ATE91406T1 (de) 1989-01-25 1990-01-17 Oberflaechenaktive mischungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3902048 1989-01-25
DE3902048A DE3902048A1 (de) 1989-01-25 1989-01-25 Oberflaechenaktive mischungen

Publications (2)

Publication Number Publication Date
EP0455657A1 EP0455657A1 (fr) 1991-11-13
EP0455657B1 true EP0455657B1 (fr) 1993-07-14

Family

ID=6372698

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90901802A Expired - Lifetime EP0455657B1 (fr) 1989-01-25 1990-01-17 Melanges tensio-actifs

Country Status (7)

Country Link
EP (1) EP0455657B1 (fr)
JP (1) JPH04503060A (fr)
AT (1) ATE91406T1 (fr)
DE (2) DE3902048A1 (fr)
ES (1) ES2058890T3 (fr)
PT (1) PT92930A (fr)
WO (1) WO1990008531A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106232767A (zh) * 2014-03-31 2016-12-14 艺康美国股份有限公司 使用醇醚磺酸盐和阳离子表面活性剂的表面活性剂辅助的油采收
US9862882B2 (en) 2015-03-03 2018-01-09 Ecolab Usa Inc. Foam assisted liquid removal using alcohol ether sulfonates

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4122200A1 (de) * 1991-07-04 1993-01-07 Henkel Kgaa Waessrige zubereitungen oberflaechenaktiver substanzen
US5275761A (en) * 1992-04-15 1994-01-04 Helene Curtis, Inc. Conditioning shampoo composition and method of preparing and using the same
ZA931613B (en) * 1992-04-15 1993-11-15 Curtis Helene Ind Inc Conditioning shampoo composition and method of preparing and using the same
CA2092284C (fr) * 1992-04-15 2003-02-11 Wolfgang Bergmann Shampooing revitalisant, methode de preparation et d'utilisation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3725030A1 (de) * 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
DE3822997A1 (de) * 1988-07-07 1990-01-18 Henkel Kgaa Detergensmischung aus nichtionischen und anionischen tensiden und deren verwendung

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106232767A (zh) * 2014-03-31 2016-12-14 艺康美国股份有限公司 使用醇醚磺酸盐和阳离子表面活性剂的表面活性剂辅助的油采收
US10400157B2 (en) 2014-03-31 2019-09-03 Ecolab Usa Inc. Surfactant assisted oil recovery using alcohol ether sulfonates and cationic surfactants
CN106232767B (zh) * 2014-03-31 2021-01-08 艺康美国股份有限公司 使用醇醚磺酸盐和阳离子表面活性剂的表面活性剂辅助的油采收
US9862882B2 (en) 2015-03-03 2018-01-09 Ecolab Usa Inc. Foam assisted liquid removal using alcohol ether sulfonates

Also Published As

Publication number Publication date
DE3902048A1 (de) 1990-07-26
WO1990008531A3 (fr) 1990-11-01
PT92930A (pt) 1990-07-31
WO1990008531A2 (fr) 1990-08-09
JPH04503060A (ja) 1992-06-04
ATE91406T1 (de) 1993-07-15
EP0455657A1 (fr) 1991-11-13
ES2058890T3 (es) 1994-11-01
DE59001972D1 (de) 1993-08-19

Similar Documents

Publication Publication Date Title
DE68905770T2 (de) Topische zusammensetzung.
EP0681469B1 (fr) Melanges tensioactifs contenant un copolymere temporairement cationique
DE68905771T2 (de) Topische zusammensetzung.
DE2057353B2 (de) Flüssige Wasch- und Reinigungsmittel
DE3726094C2 (de) Verfahren zum Entfernen von quartärem Mono-(C¶1¶¶2¶-bis C¶1¶¶8¶)-alkylammonium-Haarkonditionierer von Haar und Haarreinigungsmittel
DE69416159T2 (de) Isethionatester von alkylalkoxycarbonsäuren als milde tenside
DE69431793T2 (de) Waschmittelzusammensetzung
EP0681468B1 (fr) Melanges tensioactifs
WO1991015192A1 (fr) Melanges tensioactifs aqueux a bonne compatibilite dermique
EP0455657B1 (fr) Melanges tensio-actifs
EP0371339B1 (fr) Mélanges surfactifs
EP0508038B1 (fr) Sulfosuccinates d'esters d'acide citrique, d'alcools gras et d'éthers polyglycoliques, procédé pour leur préparation et leur utilisation
EP0602078B1 (fr) Detergents doux
EP0075906A2 (fr) Agent pour le nettoyage de cheveux et de corps avec une teneur en alkylsulfatobétaines
EP0641377B1 (fr) Melanges de tensioactifs doux
DE4213520A1 (de) Verfahren zur dauerhaften Verformung von Haaren
EP0036625A1 (fr) Agents de nettoyage liquides
WO1999010461A1 (fr) Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras
WO1993016156A1 (fr) Melanges de detergents aqueux remarquablement bien toleres par la peau
WO1992018470A1 (fr) Sulfosuccinates de polyglycolether de monoglyceride d'acide gras, leur procede de preparation et leur utilisation
DE4121612A1 (de) Waessrige tensidzubereitungen
WO1991013960A1 (fr) Melanges tensio-actifs
EP0605503A1 (fr) Preparations pour le traitement des cheveux.
WO1990007922A2 (fr) Melanges tensio-actifs
WO2017198537A1 (fr) Compositions aqueuses de tensioactif

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19910717

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE ES FR GB IT LI LU NL SE

17Q First examination report despatched

Effective date: 19920901

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE ES FR GB IT LI LU NL SE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19930714

REF Corresponds to:

Ref document number: 91406

Country of ref document: AT

Date of ref document: 19930715

Kind code of ref document: T

ET Fr: translation filed
REF Corresponds to:

Ref document number: 59001972

Country of ref document: DE

Date of ref document: 19930819

ITF It: translation for a ep patent filed
GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 19930913

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19940117

Ref country code: AT

Effective date: 19940117

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19940118

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19940131

Ref country code: LI

Effective date: 19940131

Ref country code: CH

Effective date: 19940131

Ref country code: BE

Effective date: 19940131

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
BERE Be: lapsed

Owner name: HENKEL K.G.A.A.

Effective date: 19940131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940801

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19940117

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19940930

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19941001

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2058890

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 19990405

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050117